title: In vitro evaluation of caffeoyl and cinnamoyl derivatives as potential prolyl oligopeptidase inhibitors.
abstract: A screening of the natural product chlorogenic acid, isolated from the Brazilian medicinal plant Hypericum brasiliense, caffeic acid, cinnamic acid, and p-methoxycinnamic acid, and derivatives of caffeoylquinic, caffeoyl, and cinnamoyl against the enzymes prolyl oligopeptidase and dipeptidyl peptidase IV was carried out. Caffeoylquinic, caffeoyl, and cinnamoyl derivatives were prepared using simple derivatization procedures and through coupling reactions with the amino acid proline. The dipeptidyl peptidase IV assay showed inhibitory activity of the tested compounds at a high concentration (500 µM) in the range of 81.5-7.2 %. In contrast, the derivatives methyl ester and 1,7-acetonide obtained from chlorogenic acid, and caffeic acid and its methyl ester derivative showed selectivity and activity as prolyl oligopeptidase inhibitors, with IC50 values of 3 to 14 mM.
authors.affiliation: Núcleo de Pesquisa de Produtos Naturais (NPPN), Chemistry Department, Universidade Federal de Santa Maria, Santa Maria - RS, Brazil.
authors.forename: Luciana O
authors.initials: LO
authors.lastname: Adolpho
authors.forename: Daniele
authors.initials: D
authors.lastname: Marin
authors.forename: Albert
authors.initials: A
authors.lastname: Puigpinos
authors.forename: Laura
authors.initials: L
authors.lastname: Mendieta
authors.forename: Teresa
authors.initials: T
authors.lastname: Tarragó
authors.forename: Ademir F
authors.initials: AF
authors.lastname: Morel
authors.forename: Ernest
authors.initials: E
authors.lastname: Giralt
authors.forename: Ionara I
authors.initials: II
authors.lastname: Dalcol
mesh_terms: D002109:Caffeic Acids / Q000737:chemistry* / Q000302:isolation & purification; D002934:Cinnamates / Q000737:chemistry* / Q000302:isolation & purification; D018819:Dipeptidyl Peptidase 4 / Q000737:chemistry* / Q000302:isolation & purification; D013058:Mass Spectrometry; D019906:Nuclear Magnetic Resonance, Biomolecular; D009904:Optical Rotation; D000085822:Prolyl Oligopeptidases; D012697:Serine Endopeptidases / Q000737:chemistry*; D015842:Serine Proteinase Inhibitors / Q000737:chemistry*
chemical_list: D002109:Caffeic Acids; D002934:Cinnamates; D015842:Serine Proteinase Inhibitors; C029010:cinnamic acid; D018819:Dipeptidyl Peptidase 4; D012697:Serine Endopeptidases; D000085822:Prolyl Oligopeptidases